(7aS,11aR)-2-(4-Methoxy-2-trifluoromethyl-phenyl)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3',4':4,5]pyrrolo[3,2,1-ij]quinoline

ID: ALA2337102

PubChem CID: 59012632

Max Phase: Preclinical

Molecular Formula: C22H23F3N2O

Molecular Weight: 388.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(C(F)(F)F)c1

Standard InChI:  InChI=1S/C22H23F3N2O/c1-28-15-4-5-16(19(11-15)22(23,24)25)14-9-13-3-2-8-27-20-6-7-26-12-18(20)17(10-14)21(13)27/h4-5,9-11,18,20,26H,2-3,6-8,12H2,1H3/t18-,20-/m0/s1

Standard InChI Key:  YLYUXVJVGYRALA-ICSRJNTNSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   18.3565   -3.7268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3554   -4.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0616   -3.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0599   -4.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0554   -5.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7624   -6.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4756   -5.7782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4817   -4.9557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7702   -3.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7705   -4.5419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5487   -3.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0469   -4.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9435   -4.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3488   -3.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8506   -2.6092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9471   -2.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1326   -2.7570    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.5070   -5.0228    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.6508   -3.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6519   -2.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9449   -2.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2363   -2.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2392   -3.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9467   -3.7268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3599   -2.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0673   -2.5014    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.3606   -1.2751    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.0637   -1.6757    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.5280   -2.0933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5267   -1.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  4  1  0
  9  3  2  0
  3  1  1  0
 10  4  2  0
 10  8  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  9 10  1  0
 11  9  1  0
 12  8  1  0
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 11 17  1  1
 12 18  1  1
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  1 19  1  0
 20 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 22 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2337102

   CID 59012632

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 388.43

Molecular Weight (Monoisotopic): 388.1762

AlogP: 4.59

#Rotatable Bonds: 2

Polar Surface Area: 24.50

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.64

CX LogP: 4.22

CX LogD: 2.01

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.81

Np Likeness Score: -0.24

References

1. Fevig JM, Feng J, Rossi KA, Miller KJ, Wu G, Hung CP, Ung T, Malmstrom SE, Zhang G, Keim WJ, Cullen MJ, Rohrbach KW, Qu Q, Gan J, Pelleymounter MA, Robl JA..  (2013)  Synthesis and SAR of 2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-ones as 5-HT2C receptor agonists.,  23  (1): [PMID:23177783] [10.1016/j.bmcl.2012.10.091]

Source

Source(1):

• Scientific Literature